CN113387936A - Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same Download PDF

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CN113387936A
CN113387936A CN202110122153.3A CN202110122153A CN113387936A CN 113387936 A CN113387936 A CN 113387936A CN 202110122153 A CN202110122153 A CN 202110122153A CN 113387936 A CN113387936 A CN 113387936A
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赵相熙
郑昭永
李美子
李琇炫
洪镇理
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

The present disclosure relates to: an organic electroluminescent compound represented by formula 2-1; a plurality of host materials including a first host material including a compound represented by formula 1 and a second host material including a compound represented by formula 2; and an organic electroluminescent device comprising the plurality of host materials. By including the organic electroluminescent compound according to the present disclosure as a single host material, or including a specific combination of the compounds according to the present disclosure as a plurality of host materials, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or improved life characteristics compared to conventional organic electroluminescent devices may be provided.

Description

Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same
Technical Field
The present disclosure relates to an organic electroluminescent compound, various host materials, and an organic electroluminescent device including the same.
Background
Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al, Eastman Kodak, Inc. (Eastman Kodak) in 1987 by using a TPD/ALq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. At present, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. However, in many applications, such as TV and lighting, OLED lifetime is insufficient and still more efficient OLEDs are needed. Typically, the higher the luminance of an OLED, the shorter the lifetime that the OLED has. Therefore, for long-term use and high resolution of displays, OLEDs having high luminous efficiency and/or long-life characteristics are required.
Various materials or concepts for the organic layers of OLEDs have been proposed in order to enhance the luminous efficiency, driving voltage and/or lifetime. However, they are not satisfactory in practical use.
Korean patent application laid-open No. 10-2017-0022865 discloses OLEDs using phenanthrooxazole and phenanthroothiazole compounds as hosts. However, the reference does not specifically disclose a particular combination of the various host materials of the present disclosure. Furthermore, there is still a need to develop host materials for improving OLED performance.
Disclosure of Invention
Technical problem
An object of the present disclosure is to provide an organic electroluminescent compound having a new structure suitable for its application to an organic electroluminescent device. It is another object of the present disclosure to provide an improved organic electroluminescent material capable of providing an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifetime characteristics. It is a further object of the present disclosure to provide an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or improved life characteristics by including a compound according to the present disclosure as a single host material, or a specific combination of compounds according to the present disclosure as a plurality of host materials.
Solution to the problem
As a result of intensive studies to solve the technical problems, the present inventors found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 2-1:
Figure BDA0002918075500000021
wherein
XaRepresents O or S;
Araand ArbEach independently represents a substituted or unsubstituted (C6-C18) aryl group, with the proviso that AraAnd ArbAt least one of which represents a substituted or unsubstituted naphthyl group; and is
R1To R6Each independently represents hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a combination thereof.
Further, the present inventors noticed that a compound having a core such as phenanthrooxazole or phenanthroothiazole has an abnormally low level of Lowest Unoccupied Molecular Orbital (LUMO) energy compared to a typical hole-type host, and studied a hole-type host capable of forming an appropriate energy gap with the above-mentioned compound. Accordingly, the present inventors found that when a combination of a compound represented by formula 1 below and a compound represented by formula 2 below is used in a light emitting layer, hole and electron characteristics are balanced by appropriate HOMO and LUMO levels, thereby providing an organic electroluminescent device having a lower driving voltage, higher light emitting efficiency, and/or longer life characteristics compared to conventional organic electroluminescent devices.
Specifically, the present inventors found that the above object can be achieved by a plurality of host materials comprising a first host material comprising a compound represented by the following formula 1 and a second host material comprising a compound represented by the following formula 2.
Figure BDA0002918075500000031
In the formula 1, the first and second groups,
X1and Y1Each independently represents-N ═ NR5-, -O-, or-S-, with the proviso that X1And Y1represents-N ═ and X1And Y1Another of (a) represents-NR5-, -O-, or-S-;
L1represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
R31and R32Each independently represents a substituted or unsubstituted (3-to 30-membered) heteroaryl;
R1represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R2to R5Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ringsA substituted or unsubstituted fused ring group of a group ring, or-L3-N(Ar1)(Ar2) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
L3each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar1and Ar2Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; and is
a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3, wherein if a to c are integers of 2 or more, each R2Each R3And each R4May be the same or different.
HAr-((L2)e-Ar2)d-----(2)
In the formula 2, the first and second groups,
HAr represents a substituted or unsubstituted (3-to 20-membered) heteroaryl group containing one or more nitrogen atoms;
L2each independently represents a substituted or unsubstituted (C6-C30) arylene group;
Ar2each independently represents a substituted or unsubstituted (C6-C30) aryl group, or the following formula 3 or 4:
Figure BDA0002918075500000041
y represents O, S, N-star, or NR21；
R21Represents a substituted or unsubstituted (C6-C30) aryl group;
R11to R18Each independently of the other represents2The site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstitutedSubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L4-N(Ar3)(Ar4) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
X31to X42Each independently represents N or CRa；
RaEach independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L.5-N(Ar5)(Ar6) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
L4and L5Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar3to Ar6Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered)To 30 membered) heteroaryl;
d represents an integer of 1 to 3, wherein if d is an integer of 2 or more, each ((L)2)e-Ar2) May be the same or different;
e represents an integer of 0 to 2, wherein if e is an integer of 2, each L2May be the same or different; and is
Is represented by2The site of ligation.
The invention has the advantages of
The organic electroluminescent compounds according to the present disclosure exhibit properties suitable for their use in organic electroluminescent devices. Further, by including the compound according to the present disclosure as a single host material, or including a specific combination of the compounds according to the present disclosure as a plurality of host materials, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or improved life characteristics compared to a conventional organic electroluminescent device may be provided, and a display device or an illumination device may be produced using the organic electroluminescent device.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the disclosure in any way.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as needed.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may include at least one compound. If necessary, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, or the like.
The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained before (e.g., before vapor deposition) in the organic electroluminescent device and a material contained after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the various organic electroluminescent materials of the present disclosure may be a combination of at least two compounds, which may be included in at least one layer of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds may be contained in the same layer or different layers by methods used in the art. For example, the at least two compounds may be evaporated in mixture or co-evaporated, or may be evaporated individually.
The term "plurality of host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material contained before (e.g., before vapor deposition) in the organic electroluminescent device and a material contained after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the various host materials of the present disclosure may be a combination of at least two host materials, and optionally may further include conventional materials included in the organic electroluminescent material. Various host materials of the present disclosure may be included in any light emitting layer constituting the organic electroluminescent device. At least two compounds included in the plurality of host materials of the present disclosure may be included together in one light emitting layer or may be included in different light emitting layers, respectively, by a method used in the art. For example, the at least two compounds may be evaporated in mixture or co-evaporated, or may be evaporated individually.
As used herein, the term "(C1-C30) alkyl" is intended to have 1 to 1A straight chain or branched chain alkyl group of 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like. The term "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. The term "(C2-C30) alkynyl" means a straight or branched chain alkynyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. The term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl and the like. The term "(3-to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7, preferably 5 to 7 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, and preferably O, S and N. The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. The term "(C6-C30) (arylene) means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20. The above (arylene) group may be partially saturated, and may contain a spiro structure. The above aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, phenanthrenyl, perylene, phenanthrenyl, and the like,
Figure BDA0002918075500000071
Mesityl, naphthonaphthyl, fluoranthenyl, spirobifluorenyl, and the like. More specifically, the above-mentioned aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, tetracenyl, pyrenyl, 1-
Figure BDA0002918075500000072
Base 2-
Figure BDA0002918075500000073
Base 3-
Figure BDA0002918075500000074
Base, 4-
Figure BDA0002918075500000075
Base 5-
Figure BDA0002918075500000076
Base 6-
Figure BDA0002918075500000077
Radical, benzo [ c]Phenanthryl, benzo [ g ]]
Figure BDA0002918075500000078
Radical, 1-benzophenanthryl, 2-benzophenanthryl, 3-benzophenanthryl, 4-benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [ a ] f]Fluorenyl, benzo [ b ]]Fluorenyl, benzo [ c)]Fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylyl, o-cumenyl, m-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl,4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 11-dimethyl-1-benzo [ a ] a]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ]]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzenesAnd [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl, 11-diphenyl-3-benzo [ c ]]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9,10, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9,10, 10-tetramethyl-9, 10-dihydro-2-phenanthryl, 9,10, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9,10, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like.
The term "(3-to 30-membered) (arylene) heteroaryl" means an (arylene) group having 3 to 30 ring backbone atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si and P. The above-mentioned heteroaryl (ene) group may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a (arylene) heteroaryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may comprise a spiro structure. The above-mentioned heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl (furazanyl), pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl groups, and fused heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzonaphthofuryl, benzofuranylthienyl, diazabenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, benzisoquinolyl, cinnolinyl, quinazolinyl, pyridyl, pyrazinyl, and the like, Benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, triazonaphthyl (triazapaphthyl), benzothiophenopyrimidyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, pyridopyrazinyl, benzofuropyridinyl, benzofuropyrimidinyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidinoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthopyrazinyl, benzodioxinyl, benzoxazolinyl, naphthopyrazinyl, naphthoquinazolinyl, dihydroacridinyl, pyridopyrazinyl, benzoxazolinyl, benzoxazolinopyridinyl, benzoxazolinyl, pyrimidyl, benzoxazolinyl, pyrimidyl, benzoxazolinyl, pyrimidyl, benzoxazolinyl, pyrimidyl, Benzopyrazinoindolyl, benzotriazolphenazinyl, imidazopyridinyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzene pyridyl, indolocarbazolyl, indenocarbazolyl, and the like. More specifically, the above-mentioned heteroaryl group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2, 3-triazin-4-yl, 1,2, 4-triazin-3-yl, 1,3, 5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolinyl (indolidinyl), 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 3-imidazopyridinyl, and the like, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalyl group, 5-quinoxalyl group, 6-quinoxalyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, azacarbazolyl-2-yl group, azacarbazolyl group, Azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho- [1,2-b ] -benzofuranyl, 2-naphtho- [1,2-b ] -benzofuranyl, 3-naphtho- [1,2-b ] -benzofuranyl, 4-naphtho- [1,2-b ] -benzofuranyl, 2-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzothiophenyl, 1, 2-naphtho- [1,2-b ] -benzofuranyl, 2, 4-naphtho, 5-naphtho- [1,2-b ] -benzofuranyl, 6-naphtho- [1,2-b ] -benzofuranyl, 7-naphtho- [1,2-b ] -benzofuranyl, 8-naphtho- [1,2-b ] -benzofuranyl, 9-naphtho- [1,2-b ] -benzofuranyl, 10-naphtho- [1,2-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-naphtho- [2,3-b ] -benzofuranyl, 3-naphtho- [2,3-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 6-naphtho- [2,3-b ] -benzofuranyl, 7-naphtho- [2,3-b ] -benzofuranyl, 8-naphtho- [2,3-b ] -benzofuranyl, 9-naphtho- [2,3-b ] -benzofuranyl, 10-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2,1-b ] -benzofuranyl, 2-naphtho- [2,1-b ] -benzofuranyl, 3-naphtho- [2,1-b ] -benzofuranyl, 4-naphtho- [2,1-b ] -benzofuranyl, 5-naphtho- [2,1-b ] -benzofuranyl, 6-naphtho- [2,1-b ] -benzofuranyl, 7-naphtho- [2,1-b ] -benzofuranyl, 8-naphtho- [2,1-b ] -benzofuranyl, 9-naphtho- [2,1-b ] -benzofuranyl, 10-naphtho- [2,1-b ] -benzofuranyl, 1-naphtho- [1,2-b ] -benzothienyl, 2-naphtho- [1,2-b ] -benzothienyl, 3-naphtho- [1,2-b ] -benzothienyl, 4-naphtho- [1,2-b ] -benzothienyl, a, 5-naphtho- [1,2-b ] -benzothienyl, 6-naphtho- [1,2-b ] -benzothienyl, 7-naphtho- [1,2-b ] -benzothienyl, 8-naphtho- [1,2-b ] -benzothienyl, 9-naphtho- [1,2-b ] -benzothienyl, 10-naphtho- [1,2-b ] -benzothienyl, 1-naphtho- [2,3-b ] -benzothienyl, 2-naphtho- [2,3-b ] -benzothienyl, 3-naphtho- [2,3-b ] -benzothienyl, 4-naphtho- [2,3-b ] -benzothienyl, a, 5-naphtho- [2,3-b ] -benzothienyl, 1-naphtho- [2,1-b ] -benzothienyl, 2-naphtho- [2,1-b ] -benzothienyl, 3-naphtho- [2,1-b ] -benzothienyl, 4-naphtho- [2,1-b ] -benzothienyl, 5-naphtho- [2,1-b ] -benzothienyl, 6-naphtho- [2,1-b ] -benzothienyl, 7-naphtho- [2,1-b ] -benzothienyl, 8-naphtho- [2,1-b ] -benzothienyl, 9-naphtho- [2,1-b ] -benzothienyl, a, 10-naphtho- [2,1-b ] -benzothienyl, 2-benzofuro [3,2-d ] pyrimidinyl, 6-benzofuro [3,2-d ] pyrimidinyl, 7-benzofuro [3,2-d ] pyrimidinyl, 8-benzofuro [3,2-d ] pyrimidinyl, 9-benzofuro [3,2-d ] pyrimidinyl, 2-benzothio [3,2-d ] pyrimidinyl, 6-benzothio [3,2-d ] pyrimidinyl, 7-benzothio [3,2-d ] pyrimidinyl, 8-benzothio [3,2-d ] pyrimidinyl, 9-benzothio [3,2-d ] pyrimidinyl, 2-benzofuro [3,2-d ] pyrazinyl, 6-benzofuro [3,2-d ] pyrazinyl, 7-benzofuro [3,2-d ] pyrazinyl, 8-benzofuro [3,2-d ] pyrazinyl, 9-benzofuro [3,2-d ] pyrazinyl, 2-benzothio [3,2-d ] pyrazinyl, 6-benzothio [3,2-d ] pyrazinyl, 7-benzothio [3,2-d ] pyrazinyl, 8-benzothio [3,2-d ] pyrazinyl, 9-benzothio [3,2-d ] pyrazinyl, 1-silafluorenyl (silafluorenyl), 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanenyl (gerafluorenyl), 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 6-benzofuro [3,2-d ] pyrazinyl, 8-benzothiophenyl [3,2-d ] pyrazinyl, 2-benzothiophenyl [3, 2-benzothiophenyl ] pyrazinyl, 2-benzothiophenyl, 2-silafluorenyl, 1-silafluo, and the like, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Further, "halogen" includes F, Cl, Br and I.
The term "fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings" means that at least one aliphatic ring having 3 to 30 ring backbone carbon atoms, preferably 3 to 25 ring backbone carbon atoms, and more preferably 3 to 18 ring backbone carbon atoms, and at least one aromatic ring having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, and more preferably 6 to 18 ring backbone carbon atoms are fused in the ring functional group. The above-mentioned fused ring group may include at least one fused ring group of benzene and at least one cyclohexane, at least one fused ring group of naphthalene and at least one cyclopentane, and the like. The carbon atoms of the fused ring group of the one or more (C3-C30) aliphatic rings and the one or more (C6-C30) aromatic rings may be replaced by at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably N, O, and S.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced by a group formed by the connection of two or more substituents. For example, the group formed by the "connection of two or more substituents" may be a pyridine-triazine. That is, a pyridine-triazine may be interpreted as a heteroaryl substituent, or a substituent in which two heteroaryl substituents are linked. The substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted heteroaryl containing one or more nitrogen atoms, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of the one or more aliphatic rings and one or more aromatic rings in the formulae of the present disclosure are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a phosphine oxide; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl unsubstituted or substituted with one or more (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of one or more (C1-C30) alkyl groups and one or more (3-to 30-membered) heteroaryl groups; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; (C1-C30) alkyl (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphine; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the disclosure, each of the one or more substituents is independently at least one selected from the group consisting of: (C1-C10) alkyl; (C6-C20) aryl; (3-to 20-membered) heteroaryl unsubstituted or substituted with one or more (C6-C20) aryl; and a di (C6-C20) arylamino group. According to another embodiment of the disclosure, each of the one or more substituents is independently at least one selected from the group consisting of: (C1-C6) alkyl; (C6-C12) aryl; (5-to 15-membered) heteroaryl unsubstituted or substituted with one or more (C6-C12) aryl; and a di (C6-C12) arylamino group. For example, each of the one or more substituents independently may be at least one selected from the group consisting of: methyl, phenyl, naphthyl, pyridyl, carbazolyl, phenylquinoxalinyl, and diphenylamino.
In the formulae of the present disclosure, the ring formed by the connection of adjacent substituents may be a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the disclosure, the number of ring backbone atoms is 5 to 20. According to another embodiment of the disclosure, the number of ring backbone atoms is 5 to 15. For example, the fused ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.
In the formulae of the present disclosure, heteroaryl, heteroarylene, and heterocycloalkyl may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Further, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, And substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.
Hereinafter, the compounds represented by formulas 1 and 2 will be described in more detail.
In formula 1, X1And Y1Each independently represents-N ═ NR5-, -O-, or-S-, with the proviso that X1And Y1represents-N ═ and X1And Y1Another of (a) represents-NR5-, -O-, or-S-. According to one embodiment of the present disclosure, X1And Y1represents-N ═ and X1And Y1The other of which represents-O-or-S-. For example, X1May be-N ═ and Y1May be-O-or-S-.
In formula 1, L1Represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group. According to one embodiment of the present disclosure, L1Represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. According to another embodiment of the present disclosure, L1Represents a single bond or an unsubstituted (C6-C18) arylene group. For example, L1May be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
In formula 1, R31And R32Each independently represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R31And R32Each independently represents a substituted or unsubstituted (5-to 25-membered) heteroaryl group. According to another embodiment of the disclosure, R31And R32Each independently represents a (5-to 18-membered) heteroaryl group that is unsubstituted or substituted with at least one of one or more (C6-C18) aryl groups and one or more (5-to 18-membered) heteroaryl groups. Specifically, R31And R32Each independently can be a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuropyridinyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group. For example, R31And R32Each independently can be a dibenzofuranyl, dibenzothiophenyl, benzofuranyl, unsubstituted or substituted with at least one of one or more phenyl and one or more pyridylPyridyl, benzonaphthofuryl, or benzonaphthothienyl.
In formula 1, R1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R1Represents a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5-to 15-membered) heteroaryl group. According to another embodiment of the disclosure, R1Represents an unsubstituted (C6-C15) aryl group, or an unsubstituted (5-to 15-membered) heteroaryl group. For example, R1May be phenyl, biphenyl, pyridyl, quinolinyl, or isoquinolinyl.
In formula 1, R2To R5Each independently represents a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (3-to 30-membered) heteroaryl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted tri (C1-C30) alkylsilyl group, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl group, substituted or unsubstituted tri (C6-C30) arylsilyl group, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ring-fused ring groups, or-L3-N(Ar1)(Ar2) (ii) a Or may be linked to an adjacent substituent to form one or more rings. For example, two R2Two R3Two R4、R2And R3、R3And R4、R5And R2And/or R5And R4May be connected to each other to form one or more loops. According to one embodiment, R2To R4Each independently represents hydrogen.
In formula 1, L3Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene.
Ar1And Ar2Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstitutedA substituted or unsubstituted fused ring group of unsubstituted (C2-C30) alkenyl, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-to 30-membered) heteroaryl.
In formula 1, a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3, wherein if a to c are integers or more, each R2Each R3And each R4May be the same or different.
According to one embodiment of the present disclosure, formula 1 may be represented by at least one of the following formulae 1-1 and 1-2.
Figure BDA0002918075500000151
In formulae 1-1 and 1-2, X1、Y1、L1、R31、R32、R1To R4And a to c are as defined in formula 1.
In formula 2, HAr represents a substituted or unsubstituted (3-to 20-membered) heteroaryl group containing one or more nitrogen atoms. According to one embodiment of the disclosure, HAr represents a substituted or unsubstituted (3-to 15-membered) heteroaryl group containing one or more nitrogen atoms. According to another embodiment of the disclosure, HAr represents an unsubstituted (5-to 15-membered) heteroaryl group containing one or more nitrogen atoms. Specifically, HAr may be pyridyl, pyrimidinyl, triazinyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pyridopyrazinyl, benzoquinazolinyl, benzoquinoxalinyl, benzofuropyrimidinyl, and the like.
In formula 2, L2Each independently represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group. According to one embodiment of the present disclosure, L2Each independently represents a substituted or unsubstituted (C6-C20) arylene group. According to another embodiment, L2Each independently represents a (C6-C20) arylene group unsubstituted or substituted with one or more (C6-C20) arylene groups. In particular, L2Each independently may be unsubstituted orPhenylene substituted with one or more naphthyl groups, naphthylene, biphenylene, phenylnaphthylene, naphthylphenylene, and the like.
In formula 2, Ar2Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or formula 3 or 4. According to one embodiment of the present disclosure, Ar2Each independently represents a (C6-C30) aryl substituted by one or more (C1-C6) alkyl groups; (C6-C30) aryl substituted with (5-to 15-membered) heteroaryl substituted with one or more (C6-C12) aryl; (C6-C30) aryl substituted with one or more di (C6-C12) arylamino groups; unsubstituted (C6-C30) aryl; or formula 3 or 4. Specifically, Ar2Each independently can be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzfluorenyl, diphenylbenzofluorenyl, phenyl substituted with one or more phenylquinoxalinyl, phenyl substituted with one or more diphenylamino, phenyl substituted with one or more naphthyl, formula 3 or 4, and the like.
In formula 3, Y represents O, S, N —, or NR21(ii) a And represents and L2The site of ligation.
In formula 3, R21Represents a substituted or unsubstituted (C6-C30) aryl group. According to one embodiment of the present disclosure, R21Represents a substituted or unsubstituted (C6-C18) aryl group. According to another embodiment of the disclosure, R21Represents an unsubstituted (C6-C12) aryl group. Specifically, R21May be phenyl, etc.
In formula 3, R11To R18Each independently of the other represents2The site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilylA substituted or unsubstituted fused ring group of a tri (C6-C30) arylsilyl group of (C3-C30) aliphatic ring(s) and (C6-C30) aromatic ring(s), or-L4-N(Ar3)(Ar4) (ii) a Or may be linked to an adjacent substituent to form one or more rings. According to one embodiment of the present disclosure, R11To R18Each independently of the other represents2The site of ligation; or represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-to 25-membered) heteroaryl. According to another embodiment of the disclosure, R11To R18Each independently of the other represents2The site of ligation; or represents hydrogen or an unsubstituted (C6-C18) aryl group. For example, R11To R18Each independently may be with L2The site of ligation; or may be hydrogen, phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, and the like.
In formula 4, X31To X42Each independently represents N or CRa. For example, X31To X42Each independently may be CRa。
RaEach independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L.5-N(Ar5)(Ar6) (ii) a Or may be linked to an adjacent substituent to form one or more rings. According to one embodiment of the present disclosure, RaEach independently represents hydrogen, or a substituted or unsubstituted (C6-C12) aryl group; or may be linked to an adjacent substituent to form one or more rings. According to the disclosureAnother embodiment of the invention, RaEach independently represents hydrogen, or an unsubstituted (C6-C12) aryl group; or may be linked to an adjacent substituent to form one or more rings. Specifically, RaEach independently may be hydrogen, phenyl, etc.; or may be linked to an adjacent substituent to form a benzene ring, etc.
L4And L5Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene.
Ar3To Ar6Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl.
In formula 2, d represents an integer of 1 to 3, wherein if d is an integer of 2 or more, each ((L)2)e-Ar2) May be the same or different. For example, d may be an integer of 2 or 3, and each ((L)2)e-Ar2) May be the same or different.
In formula 2, e represents an integer of 0 to 2, wherein if e is an integer of 2, each L2May be the same or different.
In formula 4, represents a group represented by2The site of ligation.
According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulae 2-1 to 2-3.
Figure BDA0002918075500000171
In formulae 2-1 to 2-3, A1To A24Each independently represents CR10Or N, wherein A1To A6At least one of (A) represents N, A7To A14Represents N, and A15To A24Represents N. According to one of the present disclosureExample A1To A6One to three of (A) represent N, and A1To A6The remainder of (A) represents CR10. According to another embodiment of the disclosure, A7To A14One to three of (A) represent N, and A7To A14The remainder of (A) represents CR10. According to a further embodiment of the disclosure, A15To A24Two of (A) represent N, and A15To A24The remainder of (A) represents CR10。
R10Each independently represents hydrogen or-L2-Ar2(ii) a Or two adjacent R10May be linked to each other to form one or more rings, wherein R's, if present, are more than one10Then each R10May be the same or different. According to one embodiment of the present disclosure, R10Each independently represents hydrogen or-L2-Ar2Wherein if there are more than one R10Then each R10May be the same or different. For example, R10Each independently represents hydrogen or-L2-Ar2(ii) a Or two adjacent R10May be linked to each other to form a benzofuran ring.
In formulae 2-1 to 2-3, L2、Ar2D, and e are as defined in formula 2.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
Figure BDA0002918075500000181
Figure BDA0002918075500000191
The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
Figure BDA0002918075500000201
Figure BDA0002918075500000211
Figure BDA0002918075500000221
Figure BDA0002918075500000231
Figure BDA0002918075500000241
Figure BDA0002918075500000251
Figure BDA0002918075500000261
Figure BDA0002918075500000271
Figure BDA0002918075500000281
Figure BDA0002918075500000291
Figure BDA0002918075500000301
Figure BDA0002918075500000311
Figure BDA0002918075500000321
Combinations of at least one of the compounds H-1 to H-28 and at least one of the compounds C-1 to C-325 can be used in organic electroluminescent arrangements.
According to one embodiment of the present disclosure, the present disclosure may provide a compound represented by formula 1 or a compound represented by formula 2. Specifically, the present disclosure may provide at least one of the compounds H-1 to H-28 and the compounds C-1 to C-325.
The organic electroluminescent compounds of the present disclosure may be represented by the following formula 2-1.
Figure BDA0002918075500000322
In the formula 2-1, the compound represented by the formula,
Xarepresents O or S;
Araand ArbEach independently represents a substituted or unsubstituted (C6-C18) aryl group, with the proviso that AraAnd ArbAt least one of which represents a substituted or unsubstituted naphthyl group; and is
R1To R6Each independently represents hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a combination thereof.
For example, AraAnd ArbEach independently can be unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, or naphthyl substituted with one or more phenyl groups, provided AraAnd ArbAt least one of which may be unsubstituted naphthyl or naphthyl substituted with one or more phenyl groups.
For example, R1To R6Each independently may be hydrogen, naphthyl, naphthylphenyl, or phenylnaphthyl, provided that R1To R6At least one of may beIs naphthyl, naphthylphenyl, or phenylnaphthyl.
Specifically, the compound represented by formula 2-1 may be exemplified by the following compounds, but is not limited thereto.
Figure BDA0002918075500000331
The compound represented by formula 1 according to the present disclosure may be produced by a synthetic method known to those skilled in the art, and for example, by referring to korean patent application publication No. 2017-0022865 (published 3/2/2017), etc., but is not limited thereto.
The compounds represented by formula 2 of the present disclosure may be produced by synthetic methods known to those skilled in the art. For example, a compound represented by any one of formulae 2-1 to 2-3 can be produced by referring to the following reaction schemes 1 to 3, but is not limited thereto:
[ reaction scheme 1]
Figure BDA0002918075500000341
[ reaction scheme 2]
Figure BDA0002918075500000342
[ reaction scheme 3]
Figure BDA0002918075500000343
In the reaction scheme, L2、Ar2D, and e are as defined in formula 2, and A1To A24As defined in formulae 2-1 to 2-3.
Although illustrative synthetic examples of the compounds represented by formula 2 of the present disclosure are described above, those skilled in the art will readily appreciate that they are all based on the Buchwald-Hartwig (Buchwald-Hartwig) crossCoupling reaction, N-arylation reaction, acidification montmorillonite (H-mont) mediated etherification reaction, Miyaura boronization reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd (II) -catalyzed oxidative cyclization reaction, Grignard reaction, heck reaction, dehydration cyclization reaction, SN (N-methyl) reaction1Substitution reaction, SN2Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and the above reaction proceeds even if a substituent defined in the above formula 2 but not specified in the specific synthetic example is bonded.
An organic electroluminescent device according to the present disclosure has a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.
One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes a light emitting layer and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. The second electrode may be a transflective electrode or a reflective electrode, and may be a top emission type, a bottom emission type, or a both-side emission type depending on the material. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.
The organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a plurality of organic electroluminescent materials including a compound represented by formula 1 as a first organic electroluminescent material and a compound represented by formula 2 as a second organic electroluminescent material. According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light emitting layer between the anode and the cathode, wherein the light emitting layer may include a compound represented by formula 1 and a compound represented by formula 2, preferably a plurality of host materials of the present disclosure.
The light emitting layer includes a host and a dopant, wherein the host includes a plurality of host materials, and a compound represented by formula 1 may be included as a first host compound of the plurality of host materials, and a compound represented by formula 2 may be included as a second host compound of the plurality of host materials. The weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30, even more preferably from about 40:60 to about 60:40, and still more preferably about 50: 50.
Herein, the light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. All of the first host material and the second host material may be contained in one layer, or the first host material and the second host material may be contained in respective different light emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light emitting layer may be less than 20 wt%.
The organic electroluminescent device of the present disclosure may further comprise at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound other than the various host materials of the present disclosure as at least one of a hole injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emission auxiliary material, and an electron blocking material. Further, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material, in addition to the various host materials of the present disclosure.
The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably selected from complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably from complex compounds of ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following formula 101, but is not limited thereto.
Figure BDA0002918075500000361
In formula 101, L is selected from the following structures 1 to 3:
Figure BDA0002918075500000362
R100to R103Each independently represents hydrogen, deuterium, halogen, a (C1-C30) alkyl group that is unsubstituted or substituted with deuterium and/or one or more halogens, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a cyano group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to an adjacent substituent to form one or more rings with the pyridine, such as substituted or unsubstituted quinoline, isoquinoline, benzofuropyridine, benzothienopyridine, benzothienoquinoline, or indenoquinoline;
R104to R107Each independently represents hydrogen, deuterium, halogen, a (C1-C30) alkyl group that is unsubstituted or substituted with deuterium and/or one or more halogens, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, cyano, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to an adjacent substituent(s) to form one or more rings with the benzene, e.g. substituted or unsubstituted naphthalene, fluorene, naphthalene, and the like,Dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine;
R201to R220Each independently represents hydrogen, deuterium, halogen, a (C1-C30) alkyl group that is unsubstituted or substituted with deuterium and/or one or more halogens, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be linked to an adjacent substituent to form one or more rings; and is
n represents an integer of 1 to 3.
Specific examples of the dopant compound are as follows, but are not limited thereto.
Figure BDA0002918075500000371
Figure BDA0002918075500000381
Figure BDA0002918075500000391
Figure BDA0002918075500000401
Figure BDA0002918075500000411
In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer in order to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. The hole transport layer or the electron blocking layer may also be a multilayer.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be a multi-layer in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds at the same time. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein each of the multiple layers may use multiple compounds.
In addition, the organic electroluminescent compound or various host materials according to the present disclosure may also be used for an organic electroluminescent device including Quantum Dots (QDs).
In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc., may be used.
When a wet film formation method is used, a thin film may be formed by dissolving or diffusing a material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, or the like). The solvent may be any solvent in which a material forming each layer can be dissolved or diffused and which has no problem in terms of film-forming ability.
The first and second host compounds of the present disclosure may be formed into films by the methods listed above, typically by co-evaporation or mixed evaporation. Co-evaporation is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and current is simultaneously applied to two cells to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in a crucible source prior to evaporation and an electric current is applied to a cell to evaporate the materials. In addition, if the first and second host compounds are present in the same layer or different layers in the organic electroluminescent device, the two host compounds may be formed as a film individually. For example, the second host compound may be deposited after the first host compound is deposited.
The present disclosure may provide a display system by including the compound represented by formula 2-1 or by using various host materials including the compound represented by formula 1 and the compound represented by formula 2. That is, by using the organic electroluminescent compound or various host materials of the present disclosure, a display system or a lighting system may be manufactured. Specifically, by using the organic electroluminescent compound or various host materials of the present disclosure, a display system, such as a display system for a smartphone, a tablet, a notebook, a PC, a TV, or an automobile; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, the preparation method of the compound according to the present disclosure, and the characteristics of the compound will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-295
Figure BDA0002918075500000421
Synthesis of Compound 1-1
In a flask, 2-bromo-7-chlorodibenzo [ b, d ]]Furan (10g, 35.17mmol), (4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborolan) (14g, 53.5mmol), PdCl2(PPh3)2(2.5g, 3.57mmol), and KOAc (8.78g, 89.25mmol) were dissolved in 180mL of 1, 4-dioxane, and the mixture was refluxed at 150 ℃ for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 9g of compound 1-1 (yield: 76.8%).
Synthesis of Compound 1-2
In a flask, compound 1-1(9g, 27.4mmol), 2-chloro-4 (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine (9.6g, 30mmol), K2CO3(9.46g, 68.5mmol), and Pd (PPh)3)4(1.58g, 1.37mmol) was dissolved in 137mL of toluene, 68.5mL of ethanol and 68.5mL of water, and the mixture was allowed to stand at 140 deg.CReflux for 12 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10g of compound 1-2 (yield: 75.5%).
Synthesis of Compound C-295
In a flask, compound 1-2(5g, 10.3mmol), (naphthalen-2-yl) -boronic acid (2.13g, 12.4mmol), Pd2(dba)3(417mg, 0.515mmol), S-Phos (423mg, 1.03mmol), and NaOtBu (2.5g, 25.75mmol) were dissolved in 50mL of xylene and the mixture was refluxed at 160 ℃ for 1 hour. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3.8g of compound C-295 (yield: 64.1%).
MW Melting Point
C-295 575.2 295℃
Example 2: preparation of Compound C-304
Figure BDA0002918075500000431
In a flask, compound 1-2(5g, 10.3mmol), (naphthalen-2-yl) -boronic acid (2.13g, 12.4mmol)l)、Pd2(dba)3(417mg, 0.515mmol), S-Phos (423mg, 1.03mmol), and NaOtBu (2.5g, 25.75mmol) were dissolved in 50mL of xylene and the mixture was refluxed at 160 ℃ for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.1g of compound C-304 (yield: 18.6%).
MW Melting Point
C-304 575.2 239.5℃
Example 3: preparation of Compound C-296
Figure BDA0002918075500000441
Synthesis of Compound 3-1
In a flask, 8-bromo-1-chlorodibenzo [ b, d ]]Furan (10g, 35.17mmol), (4,4,4',4',5,5,5',5' -octamethyl-2, 2' -bis (1,3, 2-dioxaborolan) (14g, 53.5mmol), PdCl2(PPh3)2(2.5g, 3.57mmol), and KOAc (8.78g, 89.25mmol) were dissolved in 180mL of 1, 4-dioxane, and the mixture was refluxed at 150 ℃ for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residue was removed using magnesium sulfateAnd (5) residual water. The residue was dried and separated by column chromatography to obtain 9.2g of compound 3-1 (yield: 78.5%).
Synthesis of Compound 3-2
In a flask, compound 3-1(9.2g, 28mmol), 2-chloro-4 (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine (10.2g, 32.2mmol), K2CO3(9.67g, 70mmol), and Pd (PPh)3)4(1.61g, 1.4mmol) was dissolved in 140mL of toluene, 70mL of ethanol and 70mL of water, and the mixture was refluxed at 140 ℃ for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10g of compound 3-2 (yield: 73%).
Synthesis of Compound C-296
In a flask, compound 3-2(5g, 10.3mmol), (naphthalen-2-yl) -boronic acid (2.13g, 12.4mmol), Pd2(dba)3(417mg, 0.515mmol), S-Phos (423mg, 1.03mmol), and K3PO4(5.47g, 25.75mmol) was dissolved in 50mL of xylene and the mixture was refluxed at 160 ℃ for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.5g of compound C-296 (yield: 75.9%).
MW Melting Point
C-296 575.2 227.4℃
Example 4: preparation of Compound C-325
Figure BDA0002918075500000451
Synthesis of Compound 4-1
In a flask, (1-chlorodibenzo [ b, d ]]Furan-2-yl) boronic acid (10g, 20.6mmol), 2-chloro-4 (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine (14g, 44.4mmol), K2CO3(14g, 101.5mmol), and Pd (PPh)3)4(2.4g, 2.03mmol) was dissolved in 200mL of toluene, 100mL of ethanol and 100mL of water, and the mixture was refluxed at 140 ℃ for 1 hour. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10g of compound 4-1 (yield: 87.9%).
Synthesis of Compound C-325
In a flask, compound 4-1(7g, 14.48mmol), (naphthalen-2-yl) -boronic acid (3.74g, 21.7mmol), Pd2(dba)3(663mg, 0.724mmol), S-Phos (595mg, 1.448mmol), and K3PO4(7.7g, 36.2mmol) was dissolved in 72mL of xylene and the mixture was refluxed at 160 ℃ for 1 hour. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.6g of compound C-325 (yield: 55.2%).
MW Melting Point
C-325 575.2 265.1℃
Example 5: preparation of Compound C-312
Figure BDA0002918075500000452
In a flask, compound 4-1(4.2g, 8.69mmol), compound 5-1(3.1g, 9.56mmol), Pd (PPh)3)4(502mg, 0.434mmol), and K2CO3(3g, 21.75mmol) was dissolved in 50mL of toluene, 25mL of ethanol and 25mL of water, and the mixture was refluxed at 130 ℃ for 8 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.8g of compound C-312 (yield: 31.8%).
MW Melting Point
C-312 651.23 201.6℃
Hereinafter, a method of producing an organic electroluminescent device (OLED) including an organic electroluminescent compound or a plurality of host materials according to the present disclosure and characteristics of the organic electroluminescent device will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.
Device examples 1 to 6: production of Red OLEDs with multiple host materials deposited according to the present disclosure as hosts
Producing an OLED according to the present disclosure. A transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomama co., LTD., japan) used on a glass substrate of an OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and then stored in isopropyl alcohol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 shown in Table 3 was introduced into one cell of the vacuum vapor deposition apparatus, and the compound HT-1 shown in Table 3 was introduced into the other cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and the compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a hole injection layer having a thickness of 10nm on the ITO substrate. Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the first host compound and the second host compound shown in table 1 below were introduced as hosts into two cells of a vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into the other cell. Two host materials were evaporated at a rate of 1:1 and a dopant material was simultaneously evaporated at different rates, and a dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopantTo form a light-emitting layer having a thickness of 40nm on the second hole transport layer. The compound ET-1 and the compound EI-1 were evaporated in a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. All materials used for producing OLEDs are at 10-6Purification was done by vacuum sublimation under torr.
Comparative examples 1 to 5: production of OLEDs comprising comparative Compounds as hosts
An OLED was produced in the same manner as in device example 1, except that only the host compound shown in table 1 below was used as a single host of the light emitting layer.
The driving voltage, the light emission efficiency and the light emission color at a luminance of 1,000 nits of the OLEDs produced in the device examples 1 to 6 and the comparative examples 1 to 5, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 5,000 nits (lifetime; T95) are provided in table 1 below.
[ Table 1]
Figure BDA0002918075500000471
As can be seen from table 1 above, OLEDs comprising a plurality of host materials comprising specific combinations of compounds according to the present disclosure have excellent driving voltage, light emission efficiency, and/or lifetime characteristics. This result is a significantly improved effect compared to an OLED using only each of the first and second bodies.
Comparative example 6: production of OLEDs comprising comparative Compounds as hosts
An OLED was produced in the same manner as in device example 1, except that only the host compound shown in table 2 below was used as a host of the light emitting layer.
Device examples 7 to 9: production of deposited compounds according to the present disclosureRed OLED as host
An OLED was produced in the same manner as in comparative example 6, except that only the host compound shown in table 2 below was used as a host of the light emitting layer.
The driving voltage, power efficiency, and emission color at a luminance of 1,000 nits for the OLEDs produced in comparative example 6 and device examples 7 to 9 are provided in table 2 below.
[ Table 2]
Figure BDA0002918075500000481
As can be seen from table 2 above, the OLED comprising the compound according to the present disclosure has superior driving voltage and power efficiency characteristics, compared to the OLED comprising the comparative compound.
The compounds used in the apparatus examples and comparative examples are shown in table 3.
[ Table 3]
Figure BDA0002918075500000491

Claims (12)

1. A plurality of host materials including a first host material including a compound represented by formula 1 below and a second host material including a compound represented by formula 2 below:
Figure FDA0002918075490000011
in the formula 1, the first and second groups,
X1and Y1Each independently represents-N ═ NR5-, -O-, or-S-, with the proviso that X1And Y1represents-N ═ and X1And Y1Another of (a) represents-NR5-, -O-, or-S-;
L1represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
R31and R32Each independently represents a substituted or unsubstituted (3-to 30-membered) heteroaryl;
R1represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R2to R5Each independently represents a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (3-to 30-membered) heteroaryl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted tri (C1-C30) alkylsilyl group, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl group, substituted or unsubstituted tri (C6-C30) arylsilyl group, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ring-fused ring groups, or-L3-N(Ar1)(Ar2) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
L3each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar1and Ar2Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; and is
a and b each independently represent an integer of 1 or 2, and c represents an integer of 1 to 3, wherein if a to c are integers of 2 or more, each R2Each R3And each R4May be the same or different;
HAr-((L2)e-Ar2)d-----(2)
in the formula 2, the first and second groups,
HAr represents a substituted or unsubstituted (3-to 20-membered) heteroaryl group containing one or more nitrogen atoms;
L2each independently represents a substituted or unsubstituted (C6-C30) arylene group;
Ar2each independently represents a substituted or unsubstituted (C6-C30) aryl group, or the following formula 3 or 4:
Figure FDA0002918075490000021
y represents O, S, N-star, or NR21；
R21Represents a substituted or unsubstituted (C6-C30) aryl group;
R11to R18Each independently of the other represents2The site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L.4-N(Ar3)(Ar4) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
X31to X42Each independently represents N or CRa；
RaEach independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilaneA group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L5-N(Ar5)(Ar6) (ii) a Or may be linked to an adjacent substituent to form one or more rings;
L4and L5Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar3to Ar6Each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl;
d represents an integer of 1 to 3, wherein if d is an integer of 2 or more, each ((L)2)e-Ar2) May be the same or different;
e represents an integer of 0 to 2, wherein if e is an integer of 2, each L2May be the same or different; and is
Is represented by2The site of ligation.
2. The plurality of host materials of claim 1, wherein the substituents of the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted heteroaryl containing one or more nitrogen atoms, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of the one or more aliphatic rings and one or more aromatic rings are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a phosphine oxide; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl unsubstituted or substituted with one or more (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of one or more (C1-C30) alkyl groups and one or more (3-to 30-membered) heteroaryl groups; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; (C1-C30) alkyl (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphine; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
3. The plurality of host materials according to claim 1, wherein the formula 1 is represented by at least one of the following formulae 1-1 and 1-2:
Figure FDA0002918075490000041
wherein X1、Y1、L1、R31、R32、R1To R4And a to c are asAs defined in claim 1.
4. The plurality of host materials according to claim 1, wherein the formula 2 is represented by at least one of the following formulae 2-1 to 2-3:
Figure FDA0002918075490000042
wherein
A1To A24Each independently represents CR10Or N, wherein A1To A6At least one of (A) represents N, A7To A14Represents N, and A15To A24Represents N;
R10each independently represents hydrogen or-L2-Ar2Wherein if there are more than one R10Then each R10May be the same or different; and is
L2、Ar2D, and e are as defined in claim 1.
5. The plurality of host materials of claim 1, wherein R31And R32Each independently is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuropyridinyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.
6. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the following compounds:
Figure FDA0002918075490000051
Figure FDA0002918075490000061
7. the plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the following compounds:
Figure FDA0002918075490000071
Figure FDA0002918075490000081
Figure FDA0002918075490000091
Figure FDA0002918075490000101
Figure FDA0002918075490000111
Figure FDA0002918075490000121
Figure FDA0002918075490000131
Figure FDA0002918075490000141
Figure FDA0002918075490000151
Figure FDA0002918075490000161
Figure FDA0002918075490000171
Figure FDA0002918075490000181
Figure FDA0002918075490000191
8. an organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of host materials according to claim 1.
9. An organic electroluminescent compound represented by the following formula 2-1:
Figure FDA0002918075490000192
wherein
XaRepresents O or S;
Araand ArbEach independently represents a substituted or unsubstituted (C6-C18) aryl group, with the proviso that AraAnd ArbAt least one of which represents a substituted or unsubstituted naphthyl group; and is
R1To R6Each independently represents hydrogen,Deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or a combination thereof.
10. The organic electroluminescent compound according to claim 9, wherein the compound represented by formula 2-1 is selected from the following compounds:
Figure FDA0002918075490000201
11. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 9.
12. The organic electroluminescent device according to claim 11, wherein the organic electroluminescent compound is contained in a light-emitting layer.
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